title: The Piancatelli rearrangement: new applications for an intriguing reaction.
abstract: Nearly forty years ago, at the University of Rome, Giovanni Piancatelli and co-workers discovered the acid-catalyzed water-mediated rearrangement of 2-furylcarbinols into 4-hydroxycyclopentenones. These motifs are core components of several pharmacologically active compounds and precursors of many natural products. The main features of this reaction are the simple experimental conditions, the stereochemical outcome and the generality of the procedure. Consequently, a re-emergence of this reaction has been seen recently, including developments of the Piancatelli rearrangement with some interesting inter- and intramolecular variants. This review will mainly focus on the general aspects of the reaction along with its more recent applications.
authors.affiliation: Department of Medicinal Chemistry, Nerviano Medical Sciences srl, Business Unit Oncology, Viale Pasteur 10, 20014 Nerviano, MI, Italy. claudia.piutti@nervianoms.com.
authors.forename: Claudia
authors.initials: C
authors.lastname: Piutti
authors.forename: Francesca
authors.initials: F
authors.lastname: Quartieri
mesh_terms: D000478:Alkylation; D000077608:Aprepitant; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic; D003517:Cyclopentanes / Q000737:chemistry*; D005663:Furans / Q000138:chemical synthesis / Q000737:chemistry*; D006801:Humans; D008956:Models, Chemical; D009025:Morpholines / Q000138:chemical synthesis; D064729:Neurokinin-1 Receptor Antagonists / Q000138:chemical synthesis; D011453:Prostaglandins / Q000737:chemistry; D013237:Stereoisomerism; D013729:Terpenes / Q000138:chemical synthesis
chemical_list: C548046:4-hydroxycyclopentenone; D003517:Cyclopentanes; D005663:Furans; D009025:Morpholines; D064729:Neurokinin-1 Receptor Antagonists; D011453:Prostaglandins; D013729:Terpenes; C544406:sargafuran; D000077608:Aprepitant; C012986:furfuryl alcohol